1. Craft the Cherry Compote: In a medium saucepan, combine your tart cherries and 1/4 cup granulated sugar. Cook over medium heat, stirring occasionally, for about 8-12 minutes until the cherries soften and the mixture thickens slightly. Remove from heat, then stir in the 1/2 teaspoon vanilla extract, almond extract (if using), and Kirsch (if desired). Set aside to cool completely while you make the cupcakes.
2. Bake the Delicious Cupcakes: Preheat your oven to 350°F (175°C) and line a 12-cup muffin tin with cupcake liners. In a large bowl, whisk together the 1 cup granulated sugar, cocoa powder, salt, baking powder, baking soda, and all-purpose flour. In a separate bowl, whisk together the vegetable oil, egg, buttermilk, and 1/2 teaspoon vanilla extract. Pour the wet ingredients into the dry, mixing until just smooth, then gently whisk in the hot water. The batter will be thin. Divide the batter evenly among the cupcake liners (about 1/4 cup each). Bake for 12-18 minutes, or until a toothpick inserted into the center comes out clean. Let them cool completely before frosting.
3. Prepare the Whipped Cream Frosting: In a large mixing bowl (using a hand mixer or a stand mixer with a whisk attachment), beat the softened cream cheese, powdered sugar, and 1 teaspoon vanilla extract until smooth and thick. While continuing to mix on medium-high speed, slowly pour in the cold heavy whipping cream. Whip until the frosting forms stiff peaks – it will be wonderfully fluffy yet firm, like a stabilized whipped cream.
4. Assemble Your Masterpiece! Using a small knife or a cupcake corer, carefully cut out a small hole from the center of each cooled cupcake. Fill each hole generously with your cooled cherry compote. You can replace a small piece of the removed cupcake back on top of the filling if you like. Frost the cupcakes with the whipped cream frosting. For the final touch, garnish each cupcake with a reserved whole cherry (from your initial selection), a drizzle of any remaining compote juice, and a sprinkle of chocolate shavings.